I did a little bit more digging. Perhaps this comment would help explain
why there is a problem:
https://github.com/eggert/tz/commit/45dcf69b45087cff50282d4da64b86a7d705ddf3#commitcomment-4602830

In release v2013e "America/Montreal" was removed from the zone.tab file,
and incorrect programs may assume that zone.tab is the only
authoritative list of valid TZs.

Quoting the aformentioned linked comment: 
> The TZ setting 'America/Montreal' should work as it did before, for all time 
> stamps after 1970.
> My guess is that PHP, or some other program that you're using, is looking at 
> zone.tab directly, under the incorrect assumption that only the strings 
> listed in zone.tab are valid TZ settings. You'd have a similar problem with 
> 'Asia/Istanbul', 'Europe/Nicosia', 'Asia/Saigon', etc.; these are all valid 
> TZ settings that are not in zone.tab. You need to track down which program is 
> making this invalid assumption, and fixing it to either (1) not insist that 
> the TZ setting be in zone.tab, or (2) not insist on using TZ settings like 
> America/Montreal and Asia/Istanbul that work but are not in zone.tab."

I noticed that `timedatectl list-timezones` also fails to list a valid
Montreal timezone, and it seems that this is a systemd util, pulling its
data from I don't know where... So maybe the bug is upstream.

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https://bugs.launchpad.net/bugs/1887107

Title:
  Missing entry for timezone database when setting timezone via the text
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